Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date Sat 25th October 2025
- Time 9:45AM EDT
- Location Cheshire, Connecticut
- Price Free - $38.10
- Races 3 races
- Distances 5km
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Event summary
Join us for the exciting Cheshire Community YMCA Harvest Trail Race and Y Cup Relay on Saturday, October 25th, 2025, set against the picturesque backdrop of historic Ives Farm in Cheshire, Naugatuck Valley. This vibrant community event features a 5K race that winds through beautiful fields and trails, perfect for participants of all ages. The race kicks off at the charming, newly remodeled barn, making it an ideal spot for friends and families to gather.
Before the main event, don’t miss the FREE Pumpkin Dash for kids under 6, starting at 9:45 AM, followed by the 5K race at 10:00 AM, and the fun-filled Y Cup Relay at 10:05 AM. Enjoy a day packed with family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, games, live music, and a fall-themed photo booth. Proceeds from the event will support the Cheshire YMCA’s community initiatives and the revitalization efforts for the Ives Farm property. Mark your calendars for this wonderful celebration of community spirit and autumn fun!
Before the main event, don’t miss the FREE Pumpkin Dash for kids under 6, starting at 9:45 AM, followed by the 5K race at 10:00 AM, and the fun-filled Y Cup Relay at 10:05 AM. Enjoy a day packed with family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, games, live music, and a fall-themed photo booth. Proceeds from the event will support the Cheshire YMCA’s community initiatives and the revitalization efforts for the Ives Farm property. Mark your calendars for this wonderful celebration of community spirit and autumn fun!
Organiser's Description
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. The all ages race will wind through the fields and trails on the property. The race will start and end at the historic barn that was recently remodeled. Proceeds from the race will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire land Trust has for the Ives Farm property.
. Prior to the race there will be a FREE Pumpkin Dash for kids under 6.
. Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
. Prior to the race there will be a FREE Pumpkin Dash for kids under 6.
. Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
Races
-
5K Trail Race
Incl. $3.10 Fee & Custom Harvest Trail Race Hat
Sat 25th October 2025 (10:00AM EDT)
$38.10
-
Y Cup Relay
Incl. $1.90 Fee & Custom Harvest Trail Race Hat
Sat 25th October 2025 (10:05AM EDT)
$16.90
Teams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 25-26 school year. This years Y Cup Relay will be run in honor of Coach Jerry Webb who was a beloved Physical Education teacher at Highland School and an active part of the Y Cup Relay since it began. His support and enthusiasm for this event was contagious and resulted in a great turn out of young runners. -
Pumpkin Dash
Incl. Finisher Medal
Sat 25th October 2025 (9:45AM EDT)
Free
A free race for kids 6 and under on the dirt roads of Ives Farm. Kids will get a chance to run through the same race finish line as all other racers.
Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
